Optical isomers of biologically interesting compounds should be regarded as two different entities because oftentimes they are transported differently, bound differently to receptors, metabolized differently and have different toxicities. Therefore, it is important to prepare optically active compounds before extensive biological and toxicological studies are initiated with a racemic mixture.
Racemic glycidyl azide has been prepared from epichlorohydrin by treatment with sodium azide and then aqueous sodium hydroxide [J. D. Ingham, W. L. Petty, and P. L. Nichols, Jr., J. Org. Chem., 21, 373 (1956)].
Sharpless et al., J. Org. Chem., 52, 667 (1987) describes that in the presence of acid catalyst, azide ion opens the epoxide ring of glycidyl p-nitrobenzoate at the C-3 position.
U.S. Pat. No. 4,303,414 issued to Frankel et al. on Dec. 1, 1981, discloses a composition containing glycidyl azides.
U.S. Pat. No. 4,408,063 issued to Baldwin on Oct. 4, 1983, discloses a process for preparing an enantiomer of epichlorohydrin which comprises treating an enantiomer of an alcohol of the formula: ##STR1## wherein Z is phenyl, monosubstituted phenyl, CF.sub.3 or C.sub.1 -C.sub.6 alkyl and X is Cl or Br, with alkali metal glycolate and removing said epihalohydrin by distillation.
U.S. Pat. No. 4,588,824 issued to Baldwin on May 13, 1986, also discloses processes for preparing (S) or (R) epihalohydrin.
U.S. Pat. No. 4,601,344 issued to Reed et al. on July 22, 1986, discloses a composition containing glycidyl azide polymer.
None of the above mentioned references suggest the chiral glycidyl azides and processes for their preparation.
In U.S. Pat. No. 4,705,799 issued to Gregory on Nov. 10, 1987, optically active oxazolidinone azides and derivatives thereof are described.